Reacción #50828

Ecuación de reacción

1-dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)-1H-imidazole

p-bromobenzyl bromide

→

NH4OH

title compound

1-(p-Bromobenzyl)-5-(3-hydroxypropyl)-1H-imidazole

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution is cooled to 0°
2. 2
   Otroammonia gas is bubbled through the reaction mixture for 5 min
3. 3
   Otrothe solvent is evaporated
4. 4
   Extracciónextracted with 50 ml of ether
5. 5
   Extracciónextracted with ethyl acetate (5×50 ml)
6. 6
   LavadoThe organic extracts are washed with water
7. 7
   Secadodried over sodium sulfate
8. 8
   Otroevaporated
9. 9
   OtroThe resulting oil is chromatographed on 530 g of silica gel with ethyl acetate

Procedimiento

A solution of 11.2 g of 1-dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)-1H-imidazole and 12.49 g of p-bromobenzyl bromide in 110 ml of acetonitrile is refluxed for 24 h. The solution is cooled to 0° and ammonia gas is bubbled through the reaction mixture for 5 min. After reacting an additional 45 min at room temperature, the solvent is evaporated. The residue is taken up in 100 ml of 1N hydrochloric acid and extracted with 50 ml of ether. The aqueous phase is adjusted to pH 8 and extracted with ethyl acetate (5×50 ml). The organic extracts are washed with water, dried over sodium sulfate and evaporated. The resulting oil is chromatographed on 530 g of silica gel with ethyl acetate:methanol:saturated NH4OH (90:5:5) to yield the title compound a) as an oil; NMR: δ5.00 (s, 2H).

Fuente